JPS63254179A - Antioxidant - Google Patents
AntioxidantInfo
- Publication number
- JPS63254179A JPS63254179A JP29726086A JP29726086A JPS63254179A JP S63254179 A JPS63254179 A JP S63254179A JP 29726086 A JP29726086 A JP 29726086A JP 29726086 A JP29726086 A JP 29726086A JP S63254179 A JPS63254179 A JP S63254179A
- Authority
- JP
- Japan
- Prior art keywords
- loofah
- lucioside
- glucopyranoside
- extract
- antioxidant
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 230000003078 antioxidant effect Effects 0.000 title claims abstract description 7
- 239000003963 antioxidant agent Substances 0.000 title claims abstract 5
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims abstract description 5
- 239000008103 glucose Substances 0.000 claims abstract description 5
- 229930182494 ginsenoside Natural products 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims abstract description 3
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical group OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims abstract 3
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 claims abstract 2
- SHZGCJCMOBCMKK-JFNONXLTSA-N L-rhamnopyranose Chemical compound C[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O SHZGCJCMOBCMKK-JFNONXLTSA-N 0.000 claims abstract 2
- PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 claims abstract 2
- 244000280244 Luffa acutangula Species 0.000 claims description 24
- 235000009814 Luffa aegyptiaca Nutrition 0.000 claims description 24
- 239000000126 substance Substances 0.000 claims description 13
- 239000001397 quillaja saponaria molina bark Substances 0.000 claims description 10
- 229930182490 saponin Natural products 0.000 claims description 10
- 150000007949 saponins Chemical class 0.000 claims description 10
- 150000008505 β-D-glucopyranosides Chemical class 0.000 claims description 8
- 239000002537 cosmetic Substances 0.000 abstract description 2
- 235000013305 food Nutrition 0.000 abstract description 2
- 244000302544 Luffa aegyptiaca Species 0.000 abstract 2
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 abstract 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical group O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 abstract 1
- 229930188894 lucyoside Natural products 0.000 abstract 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- -1 isobucnol Chemical compound 0.000 description 2
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 2
- 235000020778 linoleic acid Nutrition 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 241000251468 Actinopterygii Species 0.000 description 1
- 235000003956 Luffa Nutrition 0.000 description 1
- 241000219138 Luffa Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 241000269821 Scombridae Species 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000001458 anti-acid effect Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019688 fish Nutrition 0.000 description 1
- 229940089161 ginsenoside Drugs 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 235000021056 liquid food Nutrition 0.000 description 1
- 235000020640 mackerel Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000010507 melon oil Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000021055 solid food Nutrition 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 210000001835 viscera Anatomy 0.000 description 1
Abstract
Description
【発明の詳細な説明】
本発明者らはヘチマの抽出物につき研究を続けて来たが
、ヘチマから抽出された部分がより安全ですぐれた抗酸
作用のあることを見出し発明を完成した。 抽出に用い
られたヘチマの部位としては果実、茎９葉、つる等すべ
て可能であったが、特に果実（種子を含む）が、ヘチマ
サポニン物質の含有量が多いので最も好ましい。 ｎ−
ヘキサン等の刀りシ脂溶剤で、原お１のヘチマの乾燥粉
末な瓜脂後低級アルコールで加熱抽出し、濾過し次いで
この抽出液を減圧、蒸留して溶剤を削除する事によりヘ
チマエキスが得られる。抽出溶解に用いられる低級アル
コールとしてはメタノール、エタノールイソプロピルア
ルコール、イソブクノール、 ｎ −ブタノール、含
水アルコール、＠が含まれ、又、減圧、−：Ｉ２燥の代
りに、カラムクロマト吸着法等が用いる事が出来る。DETAILED DESCRIPTION OF THE INVENTION The present inventors have continued to research the extract of loofah, and have completed the invention after discovering that the extract from loofah is safer and has excellent anti-acid effects. All parts of loofah were used for extraction, including fruits, stems, leaves, and vines, but fruits (including seeds) are the most preferred because they have a high content of loofah saponin substances. n-
A loofah extract is obtained by heating and extracting the dry powdered melon oil of a raw loofah with a luffa solvent such as hexane, then filtering it, and then distilling this extract under reduced pressure to remove the solvent. can get. Lower alcohols used for extraction and dissolution include methanol, ethanol isopropyl alcohol, isobucnol, n-butanol, hydrous alcohol, and column chromatography adsorption methods can be used instead of reduced pressure and -:I2 drying. I can do it.
このヘチマエキスをメタノールに溶解し、シリカゲルカ
ラムクロマトで精製分別し、得られたヘチマエキスを、
核磁気共鳴、赤外剥ｌ吸収スペクトル紫外線スペクトル
、及び元素分析、更には１３Ｃ−ＮＨＲ等で４１ζ造決
定した所、一般式［１］ Ｅ ｏ ］で表ねされるサポ
ニンを含む事が判明した。This loofah extract was dissolved in methanol, purified and fractionated using silica gel column chromatography, and the obtained loofah extract was
The composition of 41ζ was determined by nuclear magnetic resonance, infrared absorption spectrum, ultraviolet spectrum, elemental analysis, and 13C-NHR, and it was found to contain saponin represented by the general formula [1] E o ]. .
［１］ギンゼノーリーｒド類
ギン−レノ・リーｒドｌＬＱ：Ｒ−グルコースーラ１１
ノースギンゼ入り−ｒドＩｔＢ１ ： Ｒ−グルコース
［Ｉ］］ルシオーリ″イド頌
［Ｉ］］ルレシオサイド
類シオシドＡ ； Ｒ１＝ ＣＲ２０Ｈ，Ｒ２＝β−Ｄ
−グルコピラノシド、Ｒ３＝ ＯＨ１Ｒ４＝ Ｈルシオ
シドＢ ｉ Ｒ１＝’Ｃ、Ｈ２’ ＯＪ−１、Ｒ２−β
−Ｄ〜グルコピラノシド、Ｒ１＝ １（、Ｉ？４ ＝
ＯＩ−１ルシオシドＣ： Ｒ１＝ ＣＨ３、Ｒ２＝β−
Ｄ−グルコピラノシド、Ｒ３＝ Ｏ？−１、Ｒ４＝ Ｈ
ルシオシドＤ；ｔ？＋＝（ｌ（０、Ｒ２＝β−Ｄ−グル
コピラノシド、Ｒ３＝１（、Ｒ４＝ ０１−ｒルシオシ
ドＥ ；Ｒ５＝ＣＨ２０１（、Ｒ２＝β−Ｄ−グルコピ
ラノシド１．Ｒ３＝Ｆ■、Ｒ＜ ＝ ＨルシオシドＦ
； Ｒ＋＝ＣＨ０，Ｒ２＝β−Ｄ−グルコピラノシド・
、Ｒ３＝Ｈ，Ｒ４＝Ｈ
ルシオシドＣ＋；Ｒ＋＝ＣＨ３、Ｒ２！＝β−Ｄ−グル
コピラノシド、Ｒ３＝Ｈ，’Ｒ４＝ＯＨルシオシドＨｉ
Ｒ＋＝ｃＨ３、Ｒ２＝β−Ｄ−グルコピラノシド、Ｒ３
＝ Ｈ、Ｒ４，＝ ＨルシオシドＩ ；ＲＬ＝ＣＩ−１
２０Ｈ１Ｒ２＝ ＨＮ Ｒ３’ ＝Ｈ，Ｒ４＝ＯＨ
（４，）
ギンゼノサイド類にはギンゼノサイドＲｇｌ＋ Ｒｅと
云う２＠と、又全く新しい構造をもったルシオサイド類
には、ＡからＩ迄名付けられた９種類のサポニン物質（
今後以下サポニン物質という）であった。これらのサポ
ニン物質は、従来公知のヘチマ、例えば達Ｍ＠、長糸瓜
種、トカドヘチマ等にも等しく含まれていた。抽出され
たヘチマエキス又、ヘチマエキスを形成している前記の
各サポニン物質につき、其の抗酸化性を検討したが、其
の効果は大小があったが、何れもすぐれたものであった
。[1] Ginzenorhi rd class Gin-Reno rd LQ: R-glucola 11
ItB1: R-glucose [I]] Lucioli'ide [I]] Ruresiosides Sioside A; R1 = CR20H, R2 = β-D
-Glucopyranoside, R3= OH1R4= H lucioside B i R1='C, H2' OJ-1, R2-β
-D~glucopyranoside, R1=1(,I?4=
OI-1 Lucioside C: R1=CH3, R2=β-
D-glucopyranoside, R3=O? -1, R4=H
Lucioside D;t? +=(l(0, R2=β-D-glucopyranoside, R3=1(, R4= 01-rlucioside E; R5=CH201(, R2=β-D-glucopyranoside 1. R3=F■, R<= H lucioside F
; R+=CHO, R2=β-D-glucopyranoside・
, R3=H, R4=H Lucioside C+; R+=CH3, R2! =β-D-glucopyranoside, R3=H,'R4=OH lucioside Hi
R+=cH3, R2=β-D-glucopyranoside, R3
= H, R4, = H lucioside I; RL=CI-1
20H1R2= HN R3' =H, R4=OH (4,) Ginsenosides include 2@ called ginsenoside Rgl+ Re, and luciosides with completely new structures include nine types named from A to I. Saponin substances (
(hereinafter referred to as saponin substances). These saponin substances were equally contained in conventionally known loofahs, such as Datsu M@, Long Silk Melon Seed, and Tokado Loofah. The antioxidative properties of the extracted loofah extract and each of the saponin substances forming the loofah extract were examined, and although their effects varied in magnitude, they were all excellent.
本発明によるヘチマエキス、又はサポニン物質は、アル
コール溶液又は、溶液を蒸発乾固して得られる粉末収態
で、使用する事が出来る。The loofah extract or saponin substance according to the present invention can be used in the form of an alcoholic solution or a powder obtained by evaporating the solution to dryness.
特に、プロピレングリコール溶液が水、又は油への溶解
性も良く好ましい。 該粉末、溶液を常法に従って適時
固体、又は液体の食品に混合、又食品を該溶液中に浸漬
、又は塗布して用いる事が出来る。又、化粧品において
は界面活牲剤、グリセリン等の多価アルコール、油脂１
等と併用し溶液エマルジョン、クリーム状にして使用す
る事が出来る。使用量としては、一般にヘチマエキスと
して ０．００５〜１％、各サポニン物質としては０゜
００２〜０．５％の範囲で好ましくはヘチマエキスとし
て０．０１〜１％、サポニン物質としては、０゜００５
〜０．５％で優れた抗酸化作用が認められる。In particular, a propylene glycol solution is preferred since it has good solubility in water or oil. The powder or solution can be mixed with a solid or liquid food according to a conventional method, or the food can be immersed or coated in the solution. In addition, in cosmetics, surfactants, polyhydric alcohols such as glycerin, oils and fats 1
It can be used in combination with other substances to form a solution emulsion or cream. The amount used is generally 0.005 to 1% as loofah extract, 0.002 to 0.5% for each saponin substance, preferably 0.01 to 1% as loofah extract, and 0.002 to 0.5% for each saponin substance.゜005
Excellent antioxidant effect is observed at ~0.5%.
実施例及び試験例をあげて詳Ｒ・Ｉｌｌに説明する。This will be explained in detail by giving examples and test examples.
［本発”明品の製造］
ヘチマの葉及び茎を乾燥し含水率１％以下の物を約１０
０ｇ採取し、ｎ〜ヘキサンでｊ脱脂後メタノール約１１
Ｘ８を加え６０°Ｃで約５時間加熱抽出する。次いで、
この抽出液を真空度０．１’ｌ’ｏｒｒで減圧！ｉ＋２
燥し、約２．５ｇのＪ＋１＋出物を得た。又、此のヘチ
マエキスをメタノールに溶解し、シリカゲルカラムクロ
マトで精製分別し、下記に示す成分を分別した。[Manufacture of products of the present invention] Dry loofah leaves and stems with a moisture content of 1% or less.
0g was collected, and after defatting with n~hexane, methanol approx. 11
Add X8 and heat extraction at 60°C for about 5 hours. Then,
Reduce the pressure of this extract with a vacuum degree of 0.1'l'orr! i+2
After drying, about 2.5 g of J+1+ product was obtained. In addition, this loofah extract was dissolved in methanol, purified and fractionated using silica gel column chromatography, and the components shown below were separated.
ルシオサイドＥ
１”ｔ４＝Ｈ” ）
ＩＬ４＝＝’＋１）
［試＠１］
リノール酸（和光純薬製ＨＯｇに上記の方法で得られた
ヘチマエキスの１０％プロピレングリコール溶液を０．
１ｇ加えたもの［実施例１］、又上記の方法で得られた
ルシオサイドＥ、及びルシオサイド゛Ｆの、１０％プロ
ピレングリコール溶液を一ル溶液を０．０５ｇ加えたも
の［実施例１１ ］ルシオサイドＦの１０％プロピレン
グリコール溶液を０．０５８加えたもの［実施例Ｉｌｌ
コを、１２ｏ０ｃニ保ちながらエアーポンプで連続して
、５時間通気を行った。Lucioside E 1"t4=H") IL4=='+1) [Test @1] Linoleic acid (10% propylene glycol solution of loofah extract obtained by the above method was added to HOg manufactured by Wako Pure Chemical Industries, Ltd. at 0.0%.
Lucioside E obtained by the above method and Lucioside F obtained by adding 0.05 g of a 10% propylene glycol solution [Example 11] Lucioside F. 0.058 of a 10% propylene glycol solution [Example Ill
Aeration was continuously performed using an air pump for 5 hours while maintaining the temperature at 12oC.
常法［日本薬学全編、汎用衛生試演と解説第６版６１〜
６２頁、１９７６ 年］により各紙た［の過酸物価（ｐ
ｏｖ）を測定した。Conventional Law [Complete Japanese Pharmacy, General Hygiene Demonstration and Explanation 6th Edition 61~
62, 1976], the peroxide value (p
ov) was measured.
対照例としては、ヘチマエキス又はルシオサイドＥ、及
びルシオサイドＦを添加しない同じリノール酸について
同様に行った結果を第１表に示す。As a control example, Table 1 shows the results of similar tests using loofah extract, Lucioside E, and the same linoleic acid without adding Lucioside F.
ｐｏｖ上昇抑制率（％）＝ａ−ｂ Ｘ ＩＱ。POV increase suppression rate (%) = a-b X IQ.
ａ）＝対１１（１例のＸ時間後のｐｏｖ一対１６例の０
時間ｐｏｖ
ｂ）＝実施例のＸ時間後のＰＯ■一実施例の０時間ｐｏ
ｖ
［試験ＩＩ ］
鰺の腹を開き内蔵を除去し尾部の身１／４を切断して具
の過酸化質脂ｆ＆を八木法により測定した。a) = vs. 11 (pov after X hours in 1 case vs. 0 in 16 cases)
Time pov b) = PO after X hours of example ■ 0 hour po of one example
v [Test II] The belly of the mackerel was opened, the internal organs were removed, and 1/4 of the tail was cut off, and the peroxide fat f& of the filling was measured by the Yagi method.
残部３／４を中央より縦方向に両断し、一方の半身を前
記実施例Ｎ］及び［＋１］で使用したヘチマ抽出物、及
びルシオサイドＥの１０％プロピレングリコール溶液１
００ｇを水約１ＯＬに溶解した水溶液を作成し、各々の
水溶液中に約１０分間浸漬し、ヘチマ抽出物の場合を［
実施例ＩＶ ］ルシオサイドの場合を［実施例■］とし
た。The remaining 3/4 was bisected in the longitudinal direction from the center, and one half was divided into 10% propylene glycol solution 1 of the loofah extract and Lucioside E used in Examples N] and [+1] above.
Prepare an aqueous solution by dissolving 00g in about 1OL of water, immerse it in each aqueous solution for about 10 minutes, and in the case of loofah extract [
Example IV] The case of lucioside was designated as [Example ■].
他方［実施例ＩＶ ］及び［実施例■］に於て試験に供
した残りの半身につき浸漬処理しないものを比手 続
補 止 書
較に用いた。各事例共日光直射下で干物にし、八木法に
より過酸化脂質量を測定した。On the other hand, the remaining half of the body tested in [Example IV] and [Example ■], which was not subjected to immersion treatment, was used for comparison. In each case, the fish were dried under direct sunlight, and the amount of lipid peroxide was measured using the Yagi method.
結果を第２表に示す。The results are shown in Table 2.
昭和６３年１月ノJanuary 1986
Claims (1)
び（II）で表わされるヘチマサポニン物質の中から選ば
れた１種、又は２種以上のヘチマサポニン物質を含む前
記（１）項の抗酸化剤 ［ I ］ギンゼノサイド類 ▲数式、化学式、表等があります▼ （式中Ｒ：グルコース又はグルコースラムノース） ［II］ルシオサイド類 ▲数式、化学式、表等があります▼ （式中Ｒ＿１＝ＣＨ＿３、ＣＨ＿２ＯＨ、ＣＨＯ Ｒ＿２＝Ｈ、β−Ｄ−グルコピラノシド Ｒ＿３＝Ｈ、ＯＨ Ｒ＿４＝Ｈ、ＯＨである。）[Scope of Claims] 1) An antioxidant comprising a composition extracted from loofah; 2) An antioxidant selected from loofah saponin substances extracted from loofah and represented by general formulas (I) and (II) shown below. [I] Ginsenosides ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼ (In the formula, R: glucose or glucose rhamnose) [ II] Luciosides▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, R_1=CH_3, CH_2OH, CHO R_2=H, β-D-glucopyranoside R_3=H, OH R_4=H, OH.)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP29726086A JPS63254179A (en) | 1986-12-13 | 1986-12-13 | Antioxidant |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP29726086A JPS63254179A (en) | 1986-12-13 | 1986-12-13 | Antioxidant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63254179A true JPS63254179A (en) | 1988-10-20 |
Family
ID=17844221
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP29726086A Pending JPS63254179A (en) | 1986-12-13 | 1986-12-13 | Antioxidant |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63254179A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2707646A1 (en) * | 1993-07-15 | 1995-01-20 | Univ Toulouse | Process for the extraction and purification of hemolytic saponins. |
| KR101244653B1 (en) * | 2010-06-30 | 2013-03-18 | 바이오스펙트럼 주식회사 | Compositions for Improving Skin Conditions Comprising Ginsenoside Rb3 as an Active Ingredient |
-
1986
- 1986-12-13 JP JP29726086A patent/JPS63254179A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2707646A1 (en) * | 1993-07-15 | 1995-01-20 | Univ Toulouse | Process for the extraction and purification of hemolytic saponins. |
| WO1995002606A1 (en) * | 1993-07-15 | 1995-01-26 | Universite Paul Sabatier (Toulouse Iii) | Haemolytic saponin extraction and purification method |
| KR101244653B1 (en) * | 2010-06-30 | 2013-03-18 | 바이오스펙트럼 주식회사 | Compositions for Improving Skin Conditions Comprising Ginsenoside Rb3 as an Active Ingredient |
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